1-(4-methoxybenzylidene)-5-methyl-4,5-dihydro-3H-1λ⁵-pyrazol-3-one | 24535-02-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(4-methoxybenzylidene)-5-methyl-4,5-dihydro-3H-1λ⁵-pyrazol-3-one
• 英文别名: Anhydro-1-(p-methoxy-benzyliden)-3-hydroxy-5-methyl-2-pyrazolinium-hydroxid；1-(4-methoxy-benzylidene)-5-methyl-3-oxo-pyrazolidinium betaine；Pyrazolidinium, 1-[(4-methoxyphenyl)methylene]-5-methyl-3-oxo-, inner salt；2-[(4-methoxyphenyl)methylidene]-3-methyl-3,4-dihydropyrazol-2-ium-5-olate
• CAS: 24535-02-2
• 化学式: C₁₂H₁₄N₂O₂
• 分子量: 218.255
• InChiKey: DGYZYIVYAVLGJX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.59
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  47.66
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-(4-methoxybenzylidene)-5-methyl-4,5-dihydro-3H-1λ⁵-pyrazol-3-one 、 (E)-3-(2-hydroxyphenyl)-2-(phenylsulfonyl)acrylonitrile 以 甲苯 为溶剂， 反应 12.0h， 以35%的产率得到(1R,2S,3S)-1,3-bis(4-methoxyphenyl)-5-methyl-7-oxo-2-(phenylsulfonyl)hexahydropyrazolo[1,2-a]pyrazole-2-carbonitrile
  参考文献：
  名称：

  Reactions of 3-methyl-2-oxopyrazolidinium ylides with phenylsulfonylacrylonitriles

  摘要：

  A series of methyl oxopyrazolidinium ylides was reacted with (E)-3-(2-hydroxyphenyl)-2-(phenyl-sulfonyl)acrylonitrile and 2-phenylsulfonyl acrylonitrile to give rise to (1R,2S,3S)-5-methyl-7-oxo-1,3-p-substituteddiphenyl-2-(phenylsulfonyl)-hexahydropyrazolo[1,2-a]pyrazole-2-carbonitriles through a sequential reaction accompanying methyl pyrazolone and o-quinone methide releases possibly instead of an anticipated cycloaddition process and 1,3-dipolar cycloaddition route. All the new products were identified by means of spectral/physical characteristics including X-ray diffraction data and HRMS measurements. In addition, a plausible mechanism is proposed for hydroxyphenyl substituted acrylonitrile case. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.10.022
• 作为产物：
  描述：

  2-丁烯酸乙酯 、 4-甲氧基苯甲醛 在 一水合肼 作用下， 生成 1-(4-methoxybenzylidene)-5-methyl-4,5-dihydro-3H-1λ⁵-pyrazol-3-one
  参考文献：
  名称：

  Reactions of 3-methyl-2-oxopyrazolidinium ylides with phenylsulfonylacrylonitriles

  摘要：

  A series of methyl oxopyrazolidinium ylides was reacted with (E)-3-(2-hydroxyphenyl)-2-(phenyl-sulfonyl)acrylonitrile and 2-phenylsulfonyl acrylonitrile to give rise to (1R,2S,3S)-5-methyl-7-oxo-1,3-p-substituteddiphenyl-2-(phenylsulfonyl)-hexahydropyrazolo[1,2-a]pyrazole-2-carbonitriles through a sequential reaction accompanying methyl pyrazolone and o-quinone methide releases possibly instead of an anticipated cycloaddition process and 1,3-dipolar cycloaddition route. All the new products were identified by means of spectral/physical characteristics including X-ray diffraction data and HRMS measurements. In addition, a plausible mechanism is proposed for hydroxyphenyl substituted acrylonitrile case. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.10.022

文献信息

• Microwave-assisted regioselective [1,3]-dipolar cycloaddition of 3-methyl-2-(substitutedbenzylidene)-5-oxopyrazolidin-2-ium-1-ides to benzothiophene 1,1-dioxide
  作者：Yaşar DÜRÜST、Eda SAĞIRLI、Akın SAĞIRLI

  DOI：10.3906/kim-1502-3

  日期：——

  A series of pyrazolidinium ylides was reacted with benzothiophene 1,1-dioxide to afford (3R,5S,5aS,10bS)-3-methyl-5-substitutedphenyl-2,3,5,5a-tetrahydrobenzo[4,5]thieno[3,2-c]pyrazolo[1,2-a]pyrazol-1(10bH)-one 6,6-dioxides under microwave irradiation and their structures were identified by means of spectral/physical characteristics including X-ray diffraction data and HRMS measurements.

  一系列吡唑啉鎓叶立德与苯并噻吩 1,1-二氧化物反应，得到 (3R,5S,5aS,10bS)-3-甲基-5-取代苯基-2,3,5,5a-四氢苯并[4,5]噻吩并[微波辐射下的3,2-c]吡唑并[1,2-a]吡唑-1(10bH)-酮6,6-二氧化物及其结构通过包括X射线衍射数据和HRMS在内的光谱/物理特征进行鉴定测量。